Thiophosgene → HCID 90414964, compound

Temperature

10 °C

3-Fluorobenzene-1,2-diol (5.0 g, 39 mmol) and thiophosgene (3.3 mL, 5.0 g, 42 mmol) were combined in chloroform (50 mL), cooled to 10° C. and treated dropwise over 30 min with sodium hydroxide (10% solution; 36 g, 90 mmol) with vigorous stirring. After stirring for 2 h at ambient temperature, the chloroform was removed under vacuum, and the solid formed was collected by filtration and washed with water. The solid was dissolved in ethyl acetate (100 mL), the solution was washed with water (30 mL) and saturated NaCl (30 mL), dried (Na2SO4) and evaporated. The crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane to give the title compound (1.5 g, 77%): mp 58-59° C.; 1H NMR (400 MHz, CDCl3) δ 7.28 (m, 1H), 7.12 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −131.32; EIMS m/z 170.

1. customthe chloroform was removed under vacuum
2. customthe solid formed
3. filtrationwas collected by filtration
4. washwashed with water
5. dissolutionThe solid was dissolved in ethyl acetate (100 mL)
6. washthe solution was washed with water (30 mL) and saturated NaCl (30 mL)
7. dry with materialdried (Na2SO4)
8. customevaporated
9. customThe crude solid was purified by chromatography on silica with 0-30% ethyl acetate-hexane

ORD record

ord-66e5ced49c5a4ee3bae1b067535a8cfb

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149038B2